The Dark Side of Entrepreneurship

You decide to submit yourself to the hours, sweat, and unrelenting stress. This is not a light choice, but it is the choice you know is right. Starting a business or a company is in your blood. You are an entrepreneur. The seventeen hour workdays and extreme financial risk which you are welcoming with open arms are merely means to a greater good. There is, however, a problem. You may have made a severe miscalculation; a miscalculation which could cost you far more than your business or company. This miscalculation could cost you everything.

When my parents decided to walk down the road of entrepreneurship, they felt they were ready for the extreme hours and inherent risks. After all, how could they pass up the opportunity to live out their dream of opening a gourmet bakery? This may be their only chance to find that true fulfillment which had been eluding them all of their professional careers. It would be irresponsible of them not to chase their dream.

So many good people ask and answer all of the right questions before turning to entrepreneurship. All of the right questions except for the most important one: is your family ready for your entrepreneurship? For anybody considering joining the class of entrepreneurs, what absolutely must be considered is that every minute into the night which you spend at your business is a minute your spouse spends at home without you, alone. Every Sunday you work tirelessly to finish that presentation is a Sunday your daughter will be the only player without her father or mother at her basketball game. If you have an order due in five hours and need ten hours to complete it, your family will be the ones to halt their lives and come to your aid. A husband and wife team working those excruciatingly late hours means that their son will have to do his homework by himself or take care of his own meals. Consider all of these realities and then ask yourself again, is your family ready for your entrepreneurship?

I was certainly not ready. I was not ready to fix my own dinner or put myself to sleep. I wasn’t ready for the aloneness. Staying up until 3:00 AM on any given Saturday night packing bakery orders may have thrilled some kids but not me. Going straight from school to a candy store for hours is most boys’ dream, but it was my nightmare. I was not ready for the hours or the stress. How could I have been? I was ten.

It is imperative that I take a step back at this point and make clear that there are many practically identical stories to mine which I could have shared. I just have always found it easier to interview myself than to interview others. This article should in no way be construed as any type of judgement or disparagement of decisions made by my particular family. The generalizations discussed in this piece are just that, generalizations, and should absolutely not be automatically assumed to be in reference to my family or their entrepreneurship.

It is too easy to wonder if things would have been different had my family’s entrepreneurship never been. Would I have had a less stressful childhood or would stress have just come natural to me by a different means? It is a tempting line of thinking but one which is irrelevant. Relevancy is something which is found in present and future decisions, not past decisions. When I am sitting in my sixth year at an accounting firm and deciding if I should stick with the firm or perhaps go out on my own, then I will have some relevant questions to ask. Are my wife and kids going to be fine spending practically the whole week without seeing me? Is my son going to be ok with me missing his baseball games? I’m pretty confident I know my answer.

I implore every single Syms student who is contemplating entrepreneurship not to fall into the trap which so many entrepreneurs fall into of not considering their family’s readiness. The only practical way to do that is probably to include your family in the conversation from day one. Not considering the direct impact which your entrepreneurship would have on your family would be a potentially fatal miscalculation. All many people want is for their family to be happy. Miscalculate this decision, and it could cost you everything. It could cost you your family’s happiness.